123982-81-0

Basic information

• Product Name: (S)-3-(1-AMINO-ETHYL)-PHENOL
• Synonyms: 3-[(1S)-1-AMINOETHYL]PHENOL;(S)-3-(1-AMINO-ETHYL)-PHENOL;Phenol, 3-[(1S)-1-aminoethyl]-;S-3-Hydroxy-α-methylbenzylamine
• CAS NO: 123982-81-0
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Product Categories: pharmacetical
• Mol File: 123982-81-0.mol

Chemical Properties

• Boiling Point: 266.3 °C at 760 mmHg
• Flash Point: 114.9 °C
• Appearance: white like or light brown crystalline powder
• Density: 1.096 g/cm³
• Vapor Pressure: 0.0053mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: (S)-3-(1-AMINO-ETHYL)-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(1-AMINO-ETHYL)-PHENOL(123982-81-0)
• EPA Substance Registry System: (S)-3-(1-AMINO-ETHYL)-PHENOL(123982-81-0)

Safety Data

• Hazardous Substances Data: 123982-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-(1-AMINO-ETHYL)-PHENOL is used as a reagent for the synthesis of optically active α-arylethylamines. These α-arylethylamines are important intermediates in the development of various pharmaceutical compounds, including those with potential applications in the treatment of neurological disorders, cardiovascular diseases, and other medical conditions. The optical activity of (S)-3-(1-AMINO-ETHYL)-PHENOL ensures that the synthesized compounds have the desired stereochemistry, which is essential for their biological activity and efficacy.
Used in Chemical Synthesis:
In the field of chemical synthesis, (S)-3-(1-AMINO-ETHYL)-PHENOL serves as a versatile building block for the creation of a wide range of organic compounds. Its unique structure allows it to be used in various reactions, such as condensation, substitution, and rearrangement reactions, to produce a diverse array of products. These synthesized compounds can be further utilized in various applications, including the development of new materials, catalysts, and other specialty chemicals.
Used in Research and Development:
(S)-3-(1-AMINO-ETHYL)-PHENOL is also valuable in research and development, particularly in the field of asymmetric synthesis and chiral chemistry. Its unique stereochemistry makes it an ideal candidate for studying the effects of chirality on chemical reactivity and the development of novel synthetic methods. Additionally, it can be used as a reference compound for the development and optimization of analytical techniques, such as chiral chromatography and spectroscopy, which are essential for the characterization and analysis of chiral compounds.

InChI:InChI=1/C8H11NO/c1-6(9)7-3-2-4-8(10)5-7/h2-6,10H,9H2,1H3/t6-/m0/s1

Upstream product

• 121-71-1 3-Hydroxyacetophenone 
• 63720-38-7 3-hydroxy-α-methylbenzylamine 
• 34068-01-4 1-[3-(phenylmethoxy)phenyl]ethan-1-one 
• 50919-07-8 1-(3-methoxy-phenyl)-ethylamine 
• 50919-07-8 (S)-1-(3-methoxyphenyl)ethylamine 
• 218900-56-2 (S)-[1-(3-methoxyphenyl)ethyl]carbamic acid tert-butyl ester 
• 2454-35-5 3-acetylphenyl acetate 

Downstream Products

• 477312-35-9 (S)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester 
• 477312-33-7 (S)-trifluoromethanesulfonic acid 3-(1-tert-butoxycarbonylamino-ethyl)-phenyl ester 
• 1362627-31-3 C₂₂H₃₀N₂O₄ 
• 266369-42-0 (S)-[1-(3-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester 

Relevant articles and documents

Discovery of (S,E)-3-(2-fluorophenyl)-N-(1-(3-(pyridin-3-yloxy)phenyl) ethyl)-acrylamide as a potent and efficacious KCNQ2 (Kv7.2) opener for the treatment of neuropathic pain

Acrylamide (S)-6, a potent and efficacious KCNQ2 (Kv7.2) opener, demonstrated significant activity in two models of neuropathic pain and in the formalin test, suggesting that KCNQ2 openers may be useful in the treatment of neuropathic pain including diabetic neuropathy.

Method for separating chiral amine compound and intermediate thereof

The present invention discloses a method for separating a chiral amine compound and an intermediate thereof. The method comprises the following steps: salt forming reaction of the chiral amine compounds and a resolving agent in a solvent; the chiral amine compound is 3-(1-aminoethyl) phenol, (2R, 3S) 4-amino-1, 2, 3-cyclopentyl triol or trans-cyclohexanediamine; the resolving agent is L-alpha-amino acid, an L-alpha-amino acid derivative, D-alpha amino acid or a D-alpha amino acid derivative; the method can be used for better separation of the chiral amine compound, the method has high yield and low cost, and is suitable for industrialized production.

Method for Preparing an Optically Active 1-(3-hydroxyphenyl)ethylamine

PURPOSE: A producing method of optically active 1-(3-hydroxyphenyl)ethylamine with the optical activity is provided to economically mass produce the 1-(3-hydroxyphenyl)ethylamine. CONSTITUTION: A producing method of optically active 1-(3-hydroxyphenyl)ethylamine comprises a step of reacting racemic 1-(3-hydroxyphenyl)ethylamine, with D-tartaric acid or L-tartaric acid to obtain semi tartarate, and a step of hydrolyzing the semi tartarate to form (S)- or (R)-1-(3-hydroxyphenyl)ethylamine.

Stereoselective Metal-Free Reduction of Chiral Imines in Batch and Flow Mode: A Convenient Strategy for the Synthesis of Chiral Active Pharmaceutical Ingredients

The convenient, metal-free reduction of imines that contain an inexpensive and removable chiral auxiliary allowed for the synthesis of the immediate precursors of chiral active pharmaceutical ingredients (APIs). This protocol was carried out under batch and flow conditions to give the correspoding products in high yields with almost complete stereocontrol. In the presence of trichlorosilane, an inexpensive and nontoxic reducing agent, and an achiral Lewis base such as N,N-dimethylformamide, the formal syntheses of Rivastgmine, calcimimetic NPS R-568, and a Rho kinases inhibitor were successfully accomplished. For the first time, both the diastereoselective imine reduction and the auxiliary removal were efficiently performed in a micro- or mesoreactor under continuous-flow conditions, which paved the way towards the development of a practical process for the syntheses of industrially relevant, biologically active, enantiopure N-alkylamines.

Biocatalysts and methods for the synthesis of (S)-3-(1-aminoethyl)-phenol

The present disclosure provides engineered transaminase polypeptides having improved properties as compared to naturally occurring transaminases including the ability of converting the substrate, 3′-hydroxyacetophenone to (S)-3-(1-aminoethyl)-phenol in enantiomeric excess and high percentage conversion. Also provided are polynucleotides encoding the engineered transaminases, host cells capable of expressing the engineered transaminases, and methods of using the engineered transaminases to synthesize (S)-3-(1-aminoethyl)-phenol and related compounds useful in the production of active pharmaceutical ingredients.

PROCESSES FOR PREPARING RIVASTIGMINE, SALTS AND INTERMEDIATES THEREOF

Processes for preparing Rivastigmine, salts and intermediates thereof are disclosed. More specifically, a process for preparing S-(-)-3-[(l -dimethylamino)ethyl]-phenol is provided.

Chemoenzymatic asymmetric total synthesis of (S)-Rivastigmine using ω-transaminases

A straightforward, high-yielding, chemoenzymatic total synthesis of enantiopure (S)-Rivastigmine was developed using various ω-transaminases for the asymmetric amination of appropriate acetophenone precursors. Optimisation of the biotransformation allowed scale-up and the total synthesis of (S)-Rivastigmine. The Royal Society of Chemistry 2010.

METHOD FOR PRODUCING OPTICALLY ACTIVE AMINOALKYLPHENOLS

The invention relates to a method for the enantioselective N-acylation of aminoalkylphenols, and to a method for producing enantiomer-pure compounds of formulae (I-S) and/or (I-R).

Synthesis and structure-activity relationship of acrylamides as KCNQ2 potassium channel openers

A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the α,β-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3-morpholin-4-yl-phenyl)-ethyl]-3- (4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.

A general enantioselective synthesis of α-arylethylamines

Optically active α-arylethylamines were prepared starting from acetophenones in ≥95%ee and ≥70% overall yield using oxazaborolidine catalyzed enantioselective reduction followed by the displacement of the hydroxy group by an azide group with clean inversion under Mitsunobu reaction conditions.